Unfortunately, that isn’t the case in reality. Over the years, Sullivan has garnered a respectable online following on his Tumblr, The Impossible Cool, which is known for its simple black-and-white photos of actors, musicians, and other notable figures who may have burnt out, but certainly never faded away. Photos of Joe Strummer and B.B. King are sandwiched between portraits of Robert Redford and Thelonius Monk. The stark white background and minimal design almost make the carefully thought out site seem like a photo album of the best-dressed people of all time.

Three months ago, the photographer left his New York City home in a 1972 Mercedes 280SE. American leather luggage company Ghurka has paid him to go west and photograph their fall offerings. When he has downtime, he documents his journey on Ghurka’s Rangefinder blog, touted as a “traveling photo and video essay that spotlights the best of the American road,” and named after a Ghurka bag specifically manufactured for Leica, a brand name that makes camera nerds salivate. It’s also built on the Tumblr platform.

I always wanted to convey the spirit that you don’t have to do a certain thing or make a certain amount of money to be 'cool.'

“I’m looking at Tumblr these days as more like an entire project as opposed to daily content streams,” says Sullivan. “I like the idea of launching a Tumblr that’s almost already ‘done’ so people can go through the whole experience all at once rather than wait for new content.”

Like many popular Tumblr users, Sullivan has been able to funnel his site’s success into lucrative opportunities, and for him that means putting his photography skills to use for brands like J. Crew, Wolverine, and Cole Haan. In fact, these previous projects are what piqued Ghurka’s interest to hire him for this campaign. While a lot of planning went into the cross-country expedition, Sullivan still runs into some snags. For one, his vintage ride may not survive the odyssey.

“A 1970s Mercedes isn’t meant to be driven across the country,” he laments. “When those cars were made, speed limits were like, 45 miles-per-hour probably. Blasting down highways at 80 miles-per-hour in a Mercedes that was built before I was born is just… it’s a lot,” admits Sullivan. “By the time I made it to Louisiana, I was looking at a map of the United States and staring at this massive drive across Texas. The thought of anything happening to that car in the middle of nowhere bugged me out.”

Sullivan is also worried that the Mercedes’ old-school security systems won’t keep his camera equipment safe. So the decision is made to switch to a rental car for the trek’s next phase—a decidedly less cool Ford Edge, a mid-size SUV with rounded edges and a wide grill that looks like an amalgam of an Autobot and R2-D2. What it lacks in street cred, vintage appeal, and Tumblr-ready photogenicity it makes up for with amenities like cruise control and satellite radio.

It’s actually a blessing in disguise, because now the 34-year-old photographer can focus more on finishing the campaign than worrying about things like blown gaskets and overheated carburetors. As Sullivan wraps up the last leg of the tour—a long drive from Northern California all the way to Los Angeles—he takes some time off the open road to talk about his other journey: How he went from a Tumblr blogger to a rustic photographer with a style all his own.

Do you think your experiences with the Mercedes are a microcosm for that whole “life on the Internet in photos” versus “real life” aspect?Oh totally! You can go through Tumblr and see these beautiful images of old cars. The first car we were going to use was a Land Rover Defender, and it was the same thing. They look amazing on the Internet, and then when I test-drove the thing, it was like driving a tin can. The seats were metal, they didn’t recline, and the thought of hitting 120-degree weather in the middle of the Mojave Desert was the first reason why we didn’t it. Yes, they look cool, but it reality, after you think it out, you realize you’re living in a bit of a fantasy.

How long have you been into photography and video?I started five years ago. I worked in the film business for a long time. I worked in the location department and moved up into the production world. I got burnt out on that. I’ve always taken photography seriously; I even went to school for filmmaking. I got sidetracked after college and decided to stop working and go out on my own.

When did you first move to New York?I think it was the summer of 2003. I grew up in Philly, and I graduated high school and then moved around. I didn’t know what I wanted to do so I traveled for two years, came out west, spent some time out here, then ended up back in Philly. I went to college but didn’t finish, so I left and moved up to New York.

I always visited New York when I was younger because Philly was so close. I was a skater and that was one of the other cities we went to skate, and write graffiti. I’ve lived in New York for the past ten years. I plan on moving to California, but I’m keeping my place in New York. I want to head out there and really get my feet wet. There’s a lot to do out in LA, so after this trip I’m going to give it a try.

When did you join Tumblr?I joined it when it first launched, sometime around June 2007. I had a Blogspot at the time, but didn’t want to do Wordpress because it felt dirty. This really started out as something I just did for fun. Tumblr at that time was the easiest platform to use: It was very user friendly. Another thing was that I hated the comments on the other platforms. The feedback was negative. I wanted to keep negativity away from the site. I didn’t want people to talk shit about who slept with whom. I wanted a site that really presented the people.

So there was a sense of purity about it?Exactly! You’re really just presenting it to the people. You’re not offering an opinion. You’re just giving it to people.

Was Tumblr a little bit easier for you to use as a visually oriented person?Oh yeah, totally. Whenever I mention the beginning, I always have to give a shout to Justin Saunders at JJJJound. In my memory, he was the first person to actually do the never-ending picture stream.

Yeah, Justin is a pioneer in that sense.Totally! He was doing that before Tumblr was around. I always thought that was super cool because you can start to create stories inside this photo stream—which a lot of people do now. So yes, being a visual person was also great for the Tumblr platform.

Was the idea always to post these iconic photos of celebrities?Actually, that came from when I first moved to New York. I was working for Paul Smith in the suit room, back in the old haberdashery on Fifth Avenue.